N-glycidyl compound

• US 5,280,069 A
• Filed: 04/30/1991
• Issued: 01/18/1994
• Est. Priority Date: 05/05/1990
• Status: Expired due to Fees

• Current Assignee: Huntsman Advanced Materials Americas, Inc.
• Original Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Inventors: Dobinson, Bryan, Thoseby, Michael R.
• Primary Examiner(s): KRASS, FREDERICK F
• Application Number:
  US07/693,874
• Time in Patent Office: 994 Days
• Field of Search: 525/109, 528/341, 528/363, 528/407, 528/408, 528/418, 549/552
• US Class Current: 525/109
• CPC Class Codes: C07D 303/36 with hydrocarbon radicals, substituted by nitrogen atoms nitro, nitroso radicals C07D303/08
• CPC Class Codes: C08G 59/3227 Compounds containing acyclic nitrogen atoms

Abstract

The new compound N,N,N'"'"'N'"'"'-tetraglycidyl-3,3'"'"'-diethyl-4,4'"'"'-diaminodiphenylmethane and curable resin compositions containing it.

Claims

1. A curable resin composition comprising:

a) an epoxide resin component consisting essentially of the pure specific compound N,N,N'"'"',N'"'"'-tetraglycidyl-3,3'"'"'-diethyl-4,4'"'"'-diaminophenylmethane;

b) a hardener; and

optionally,

c) a curing accelerator.

2. A composition according to claim 1, in which component b) is a nitrogen-containing compound which remains inert towards N,N,N'"'"',N'"'"'-tetraglycidyl-3,3'"'"'-diethyl-4,4'"'"'-diaminodiphenylmethane below a temperature of at least 80°

C.

3. A composition according to claim 2 in which component b) remains inert towards N,N,N'"'"',N'"'"'-tetraglycidyl-3,3'"'"'-diethyl-4,4'"'"'-diaminodiphenylmethane below a temperature of at least 100°

C.

4. A composition according to claim 1 in which component b) is a boron trichloride/amine or boron trifluoride/amine complex;

dicyandiamide;

melamine;

diallymelamine;

a guanamine;

an aminotriazole;

a hydrazide;

semicarbazide;

cyanoacetamide;

or an aromatic polyamine.

5. A composition according to claim 4 in which the guanamine is acetoguanamine or benzoguanamine;

the aminotriazole is 3-amino-1,2,4-triazole;

the hydrazide is adipic-, stearic- or isophthalic hydrazide; and

the aromatic polyamine is diaminodiphenylsulphone.

6. A composition according to claim 1 in which component b) is a polycarboxylic acid or a polycarboxylic acid anhydride.

7. A composition according to claim 6 in which the polycarboxylic acid anhydride is hexahydrophthalic anhydride or methyl tetrahydrophthalic anhydride.

8. A composition according to claim 1 in which the curable resin composition contains 1 to 60 wt. %, of hardener component b) based on the amount of component a).

9. A composition according to claim 8 in which the curable resin composition contains 5 to 50 wt. % of hardener component b), based on the amount of component a).

10. A composition according to claim 1 in which the curable resin composition contains 0 to 15 wt. % of component c), based on the weight of component a).

11. A composition according to claim 10 in which the curable resin composition contains 0 to 10 wt. % of component c), based on the weight of component a).

12. A composition according to claim 1 in which one or more of plasticizer, an inert diluent or a reactive diluent are also present.

13. A composition according to claim 1 in which one or more of a filler, a reinforcing material, a polymeric toughening agent, a colouring agent, a flow-control agent, a flame retardant or a mould lubricant is also present.

14. A laminating-, impregnating- or casting resin, a powder coating, a moulding composition, a putty or sealing compound, or a potting or electrically insulating compound comprising the composition of claim 1.

15. A composition according to claim 1, in which the curing accelerator is present and is a latent Lewis acid complex, a base or a latent base.

16. A composition according to claim 15, in which the curing accelerator is a BF₃ -amine complex;

a substituted urea;

or a tertiary amine or a complex thereof with BCl₃.

17. A composition according to claim 16, in which the BF₃ -amine complex is a BF₃ -ethylamine complex and the substituted urea is monuron or chlortoluron.

18. A composition according to claim 15, in which the curing accelerator is a solid solution of a nitrogen base having a boiling point above 130°

C. and a phenolic polymer which is an addition polymer of a phenol bearing an unsaturated substituent;

or a reaction product of a nitrogen base and a halogen-substituted monomeric phenol.